Identification
YMDB ID: YMDB00656
Name: D-glucitol
Species: Saccharomyces cerevisiae
Strain: Baker's yeast
Description: Sorbitol (glucitol) is a six-carbon sugar alcohol found in apples, pears, peaches, and prunes. It is synthesized by sorbitol-6-phosphate dehydrogenase, and converted to fructose by succinate dehydrogenase and sorbitol dehydrogenase. Succinate dehydrogenase is an enzyme complex that participates in the citric acid cycle.
Structure: Thumb
Download: MOL | SDF | SMILES | InChI
Synonyms:
  • (-)-Sorbitol
  • (2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
  • 1,2,3,4,5,6-Hexanehexol
  • Cholaxine
  • clucitol
  • Cystosol
  • D-(-)-Sorbitol
  • D-1,2,3,4,5,6-hexanehexol
  • d-Galactitol
  • D-Glucitol
  • d-sorbit
  • d-Sorbite
  • D-Sorbitol
  • D-Sorbol
  • Diakarmon
  • Esasorb
  • Glucarine
  • glucitol
  • Glucitol, D-
  • gulitol
  • Hexahydric alcohol
  • Hexitol
  • Karion
  • l-gulitol
  • Multitol
  • Nivitin
  • Orbit
  • Probilagol
  • Resulax
  • Sionit
  • Sionit K
  • Sionite
  • Sionon
  • Siosan
  • Sorban
  • Sorbelite C
  • Sorbicolan
  • Sorbilande
  • Sorbilax
  • sorbite
  • Sorbitol
  • Sorbitur
  • Sorbo
  • Sorbol
  • Sorbostryl
  • Sorbostyl
  • Sorvilande
Chemical Formula:
C6H14O6
Weight: Average: 182.1718
Monoisotopic: 182.07903818
InChI Key: InChIKey=FBPFZTCFMRRESA-JGWLITMVSA-N
InChI:
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1
Plain Text
CAS number: 50-70-4
IUPAC Name:
(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
Traditional IUPAC Name:
D-sorbitol
SMILES:
OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
Plain Text
Chemical Taxonomy
Kingdom: Organic Compounds
Super Class: Aliphatic Acyclic Compounds
Class: Aldehydes
Sub Class: Beta Ketoaldehydes
Other Descriptors:
  • Organic Oxonium Compounds
Substituents:
  • 1,2-diol
  • secondary alcohol
  • primary alcohol
Physical Properties
State: Liquid
Charge: 0
Melting point: 11 °C
Experimental Properties:
Property Value Source
Water Solubility: 2750 mg/mL at 30 oC [MULLIN,JW (1972)] PhysProp
LogP: -2.20 [SANGSTER (1994)] PhysProp
Predicted Properties:
Property Value Source
Water Solubility: 2.29e+02 g/l ALOGPS
LogP: -2.68 ALOGPS
LogP: -3.7300188486666666 ChemAxon Molconvert
LogS: 0.1 ALOGPS
pKa: 13.4 ChemAxon Molconvert
Hydrogen Acceptor Count: 6 ChemAxon Molconvert
Hydrogen Donor Count: 6 ChemAxon Molconvert
Polar Surface Area: 121.38 A2 ChemAxon Molconvert
Rotatable Bond Count: 5 ChemAxon Molconvert
Refractivity: 38.4 ChemAxon Molconvert
Polarizability: 17.0 ChemAxon Molconvert
Biological Properties
Cellular Locations:
  • extracellular
  • cytoplasm
Pathways:
  • Fructose and mannose metabolism 00051 Link_out
  • Galactose metabolism 00052 Link_out
Concentrations
Not Available
Details describing the conversion of literature concentrations can be found here.
Spectra
Experimental Low Energy QqQ MS/MS Spectrum view
Experimental Medium Energy QqQ MS/MS Spectrum view
Experimental High Energy QqQ MS/MS Spectrum view
Experimental 13C NMR Spectrum view
Experimental 13C HSQC Spectrum view
Experimental 1H NMR Spectrum view
Experimental 2D TOCSY Spectrum view
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160. Pubmed: 18846089 Link_out
  • Sarthy, A. V., Schopp, C., Idler, K. B. (1994). "Cloning and sequence determination of the gene encoding sorbitol dehydrogenase from Saccharomyces cerevisiae." Gene 140:121-126. Pubmed: 8125328 Link_out
Synthesis Reference: Liu, Haichao; Luo, Chen. Method for manufacturing sorbitol and mannitol with cellulose. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 8pp.
External Links:
Resource Link
CHEBI ID: 17924 Link_out
HMDB ID: HMDB00247 Link_out
Pubchem Compound ID: 5780 Link_out
Kegg ID: C00794 Link_out
ChemSpider ID: 24533858 Link_out
Wikipedia: Sorbitol Link_out
BioCyc ID: SORBITOL Link_out
Enzymes
Name: Sorbitol dehydrogenase 1
Reactions:
  • L-iditol + NAD(+) = L-sorbose + NADH.
Gene Name: SOR1 Link_out
Uniprot ID: P35497 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: NADPH-dependent aldose reductase GRE3
Reactions:
  • Alditol + NAD(P)(+) = aldose + NAD(P)H.
  • (R)-lactaldehyde + NADP(+) = methylglyoxal + NADPH.
Gene Name: GRE3 Link_out
Uniprot ID: P38715 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Not Available